4.4 Article

Syntheses of thallusin analogues and their algal morphogenesis-inducing activities

Journal

TETRAHEDRON
Volume 74, Issue 50, Pages 7173-7178

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2018.10.048

Keywords

Structure-activity relationship; Thallusin; Marine algae; Synthesis; Tandem cyclization

Funding

  1. Ministry of Education, Culture, Sports, Science and Technology (MEXT) of the Japanese Government [26460026, 18K05365]
  2. Adaptable and Seamless Technology Transfer Program through Target -driven R&D (A-STEP) of Japan Science and Technology Agency (JST) [AS231Z01199E]

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Thallusin is the only known natural product that induces cell differentiation followed by formation of a thallus during the growth of green macroalgae such as Monostroma and Ulva. Herein, various thallusin analogues based on the terpen skeleton were synthesized to study the structure-activity relationships of thallusin. The potency of the synthetic analogues was investigated in an experimental assay, which demonstrated that the 19-methyl group in thallusin is essential for potent morphogenesis-inducing activity. (C) 2018 Elsevier Ltd. All rights reserved.

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